Hydrochloric Acid → 1-(2-Chloro-4-fluoro-5-nitrophenyl)ethanone

HRID 369599

Reaktionsgleichung

Reaktionsgleichung von HRID 369599
[Cl-].C[Zn+].[Cl:4][C:5]1[CH:13]=[C:12]([F:14])[C:11]([N+:15]([O-:17])=[O:16])=[CH:10][C:6]=1[C:7](Cl)=[O:8].Cl.[CH2:19](Cl)Cl>O1CCCC1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[Cl:4][C:5]1[CH:13]=[C:12]([F:14])[C:11]([N+:15]([O-:17])=[O:16])=[CH:10][C:6]=1[C:7](=[O:8])[CH3:19]

Komponenten

7

Edukt 4

HCID 313Hydrochloric AcidHCID 6344DichloromethaneHCID 151243842-Chloro-4-fluoro-5-nitrobenzoyl chlorideHCID 178477797HCID 178477797, Verbindung

Produkt 1

HCID 183144841-(2-Chloro-4-fluoro-5-nitrophenyl)ethanone

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

A 2 M solution of methylzinc chloride in tetrahydrofuran (5.00 mL, 10.1 mmol) is treated dropwise with a solution of 2-chloro-4-fluoro-5-nitrobenzoyl chloride (2.00 g, 8.40 mmol) in tetrahydrofuran, treated with tetrakis(triphenylphosphine)palladium(0) (0.400 g, 0.350 mmol), stirred at room temperature for one hour, and poured into 3 N hydrochloric acid. The resultant aqueous mixture is extracted with ethyl acetate. The organic extracts are combined, washed sequentially with water and saturated sodium hydrogen carbonate solution, dried over anhydrous magnesium sulfate, and concentrated in vacuo to obtain a dark liquid. Flash column chromatography of the liquid using silica gel and a methylene chloride in hexanes solution (6:4) gives the title product as an off-white solid (mp 66-68° C.) which is identified by NMR spectral analyses.

Aufarbeitung

  1. extractionThe resultant aqueous mixture is extracted with ethyl acetate
  2. washwashed sequentially with water and saturated sodium hydrogen carbonate solution
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated in vacuo
  5. customto obtain a dark liquid

Quellen und Nachweise

ORD-Eintrag
ord-9d62396b67db4bc9b760b8f234fdd518
Quelldatensatz
uspto-grants-2000_10
Patentnummer
US06140270

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